Imidazole → HCID 131734478, compound

Participants

Reaction Steps

To a solution of 6-hydroxymethyl)-1,3-benzoxazol-2(3H)-one (Intermediate 77, 330 mg, 2.0 mmol) in DMF (10 mL) was added imidazole (203 mg, 2.98 mmol) and the reaction was cooled to 0° C. before tert-butylchlorodiphenylsilane (0.52 mL, 2.0 mmol) was added dropwise. Upon addition, the reaction was allowed to warm up to room temperature and stirring was maintained for 16 hours. Water and CH2Cl2 (40 mL each) were added to the reaction mixture and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×50 mL) and the resulting organic extracts were washed with water (2×50 mL) and brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The brown oil obtained was purified by column chromatography over silica gel eluting with Hexane:Et2O (from 0 to 100% of Et2O) to afford the title compound as a beige solid (437 mg, 54% yield).

Provenance & Evidence